Selenium Dioxide → HCID 68130848, compound

HRID 1657707Notes

Reaction equation

HRID 1657707 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C:10]1([O:28][CH3:29])[C:26](=[O:27])[N:12]2[CH:13]([C:18]([O:20][CH2:21][C:22]([Cl:25])([Cl:24])[Cl:23])=[O:19])[C:14]([CH3:17])=[CH:15][S:16][C@H:11]12)=[O:8].[Se](=O)=[O:31]>C(O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C:10]1([O:28][CH3:29])[C:26](=[O:27])[N:12]2[CH:13]([C:18]([O:20][CH2:21][C:22]([Cl:24])([Cl:25])[Cl:23])=[O:19])[C:14]([CH2:17][OH:31])=[CH:15][S:16][C@H:11]12)=[O:8]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 68130773HCID 68130773, compound

Product 1

HCID 68130848HCID 68130848, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of β,β,β-trichloroethyl 7-(2-thienylacetamido)-7-methoxy-3-methyl-2-cephem-4-carboxylate (0.94 mg., 2 mmole) in ethanol (10 ml.) is added selenium dioxide (0.111 g., 1 mmole) keeping the reaction temperature at about 25°C. The reaction mixture is stirred for two hours, filtered, diluted with water (30 ml.) and extracted with chloroform. The chloroform extracts are washed successively with water, sodium bicarbonate and water. The solvent is removed under vacuum to afford a residue which is chromatographed on silica gel using chloroform and ethyl acetate to afford substantially pure β,β ,β-trichloroethyl 7-(2-thienylacetamido)-7-methoxy-3-hydroxymethyl-2-cephem-4-carboxylate.

Workup

  1. customat about 25°C
  2. filtrationfiltered
  3. additiondiluted with water (30 ml.)
  4. extractionextracted with chloroform
  5. washThe chloroform extracts are washed successively with water, sodium bicarbonate and water
  6. customThe solvent is removed under vacuum
  7. customto afford a residue which
  8. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-644167f25ba345868448bee3f2b83294
Source dataset
uspto-grants-1976_06
Patent number
US03962231

Reaction notes

Loading…